JPH04318053A - Production of phenolic resin molding material - Google Patents
Production of phenolic resin molding materialInfo
- Publication number
- JPH04318053A JPH04318053A JP8430291A JP8430291A JPH04318053A JP H04318053 A JPH04318053 A JP H04318053A JP 8430291 A JP8430291 A JP 8430291A JP 8430291 A JP8430291 A JP 8430291A JP H04318053 A JPH04318053 A JP H04318053A
- Authority
- JP
- Japan
- Prior art keywords
- phenolic resin
- molding material
- molding
- calcium hydroxide
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000012778 molding material Substances 0.000 title claims abstract description 19
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 19
- 229920001568 phenolic resin Polymers 0.000 title claims abstract description 12
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 9
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 9
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 9
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 8
- 229920003987 resole Polymers 0.000 claims abstract description 8
- 239000000945 filler Substances 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000002989 phenols Chemical class 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 9
- 239000011134 resol-type phenolic resin Substances 0.000 abstract description 9
- 229930040373 Paraformaldehyde Natural products 0.000 abstract description 4
- 238000000465 moulding Methods 0.000 abstract description 4
- 239000003365 glass fiber Substances 0.000 abstract description 3
- 238000001746 injection moulding Methods 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- -1 amine compounds Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、マイクロスイッチ等の
電気部品やヒートインシュレータ等の自動車部品の成形
に適した速硬化性のフェノール樹脂成形材料の製造法に
関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a fast-curing phenolic resin molding material suitable for molding electrical parts such as microswitches and automobile parts such as heat insulators.
【０００２】0002
【従来の技術】マイクロスイッチ等の電気部品や高温で
ゴム等と接触する自動車部品をフェノール樹脂成形材料
を用いて成形する場合、腐食性のアミン化合物を発生し
ないレゾール型フェノール樹脂成形材料を使用している
。従来、レゾール型フェノール樹脂は、ホルムアルデヒ
ドとフェノール類を、ＮａＯＨ、ＫＯＨ、アンモニア等
のアルカリ触媒存在下で反応させて得たものであり、こ
れに補強や増量材としての充填材や添加剤を適宜配合し
て混練後、粉砕して成形材料としている。前記レゾール
型フェノール樹脂は硬化が遅く、その原因は、樹脂の高
分子量化が十分でなく、未反応フェノール等が多く含ま
れているためと推測される。[Prior Art] When molding electrical parts such as microswitches or automobile parts that come into contact with rubber or the like at high temperatures using phenolic resin molding materials, resol-type phenolic resin molding materials that do not generate corrosive amine compounds are used. ing. Conventionally, resol-type phenolic resins are obtained by reacting formaldehyde and phenols in the presence of an alkali catalyst such as NaOH, KOH, or ammonia, and are added with fillers and additives as reinforcing and bulking agents as appropriate. After blending and kneading, the materials are ground into a molding material. The resol type phenol resin cures slowly, and the reason for this is presumed to be that the molecular weight of the resin is not sufficiently high and that it contains a large amount of unreacted phenol.
【０００３】これを改善する方法として、（１）反応の
第１段階は酸触媒で高分子化を進め、第２段階でアルカ
リ触媒によるメチロール化を進めることが行なわれてい
る。また、（２）第１段階はアルカリ土類触媒でメチロ
ール化を進め、第２段階でアンモニア触媒による高分子
量化を進めることも行なわれている。[0003] As a method to improve this, (1) the first step of the reaction is to proceed with polymerization using an acid catalyst, and the second step is to proceed with methylolization using an alkali catalyst. Furthermore, (2) methylolization is carried out using an alkaline earth catalyst in the first step, and polymerization using an ammonia catalyst is carried out in the second step.
【０００４】0004
【発明が解決しようとする課題】上記（１）の方法で得
たフェノール樹脂は、未反応フェノールは少ないがメチ
ロール化が十分でなく、成形材料にしたときの硬化性が
十分でない。また、（２）の方法で得たフェノール樹脂
は、未反応フェノール成分がまだ多く、硬化性が十分改
善されているとはいえない。本発明が解決しようとする
課題は、レゾール型フェノール樹脂を用いた成形材料の
硬化速度を速くすることである。[Problems to be Solved by the Invention] The phenol resin obtained by the method (1) above has a small amount of unreacted phenol, but is not sufficiently methylolized and has insufficient curability when used as a molding material. In addition, the phenol resin obtained by method (2) still has a large amount of unreacted phenol components, and it cannot be said that the curability has been sufficiently improved. The problem to be solved by the present invention is to increase the curing speed of a molding material using a resol type phenolic resin.
【０００５】[0005]
【課題を解決するための手段】上記課題を解決するため
に、本発明に係るレゾール型フェノール樹脂成形材料は
、次のようにして製造する。まず、ホルムアルデヒド／
フェノール類のモル比を１．２〜１．３とし、第３級ア
ミン触媒存在下で第１段目の反応を行なわせる。その後
、アンモニア触媒存在下で第２段目の反応を行なわせて
レゾール型フェノール樹脂を得る。そして、前記レゾー
ル型フェノール樹脂に水酸化カルシウム、充填材を配合
して混合混練するものである。[Means for Solving the Problems] In order to solve the above problems, a resol type phenolic resin molding material according to the present invention is produced as follows. First, formaldehyde/
The molar ratio of phenols is set to 1.2 to 1.3, and the first stage reaction is carried out in the presence of a tertiary amine catalyst. Thereafter, a second stage reaction is carried out in the presence of an ammonia catalyst to obtain a resol type phenol resin. Then, calcium hydroxide and a filler are mixed and kneaded with the resol type phenolic resin.
【０００６】[0006]
【作用】上記のような反応のさせかたにより、硬化性に
悪影響を及ぼしていたレゾール樹脂中の未反応フェノー
ル成分を大幅に少なくすることができる。同時に、第３
級アミン触媒の使用で樹脂の熱安定性が向上するので、
成形材料とするときに硬化促進剤としての水酸化カルシ
ウムの添加を量を増やすことができ、これによって硬化
性の大幅な改善が可能となる。ホルムアルデヒド／フェ
ノール類のモル比は、１．２未満では成形材料としたと
きの硬化性が十分でなく、１．３を越えると射出成形を
するときのシリンダ安定性が低下する。[Function] By carrying out the reaction as described above, it is possible to significantly reduce the unreacted phenol component in the resol resin, which had an adverse effect on the curability. At the same time, the third
The use of grade amine catalysts improves the thermal stability of the resin.
When used as a molding material, the amount of calcium hydroxide added as a hardening accelerator can be increased, thereby making it possible to significantly improve hardenability. When the molar ratio of formaldehyde/phenols is less than 1.2, the curing property when used as a molding material is insufficient, and when it exceeds 1.3, cylinder stability during injection molding is reduced.
【０００７】[0007]
【実施例】本発明に係る実施例で使用するフェノール類
は、フェノール、クレゾール、キシレノール等の一価の
フェノール類、カテコール、レゾルシン等の多価のフェ
ノール類である。ホルムアルデヒドは、パラホルムアル
デヒド、ホルマリン等である。ホルムアルデヒド／フェ
ノール類のモル比は、好ましくは１．２５〜１．３であ
る。EXAMPLES The phenols used in the examples of the present invention are monohydric phenols such as phenol, cresol and xylenol, and polyhydric phenols such as catechol and resorcinol. Formaldehyde includes paraformaldehyde, formalin, and the like. The formaldehyde/phenols molar ratio is preferably 1.25 to 1.3.
【０００８】触媒として使用する第３級アミンは、トリ
メチルアミン、トリエチルアミン、トリエタノールアミ
ン等である。その添加量は、フェノール類とホルムアル
デヒドの合計重量に対して０．３〜１％が適当である。
少なすぎると、フェノール樹脂製造の反応速度が遅くな
る。一方、多すぎると、フェノール樹脂製造の反応が速
くなり、制御が難しくなる。また、アンモニアは、高分
子量化、硬化性の向上に必要で、その添加量は、前記両
者の合計重量に対して０．２〜１％が適当である。少な
いと、製造するフェノール樹脂の高分子量化が十分でな
く、硬化性も改善されない。尚、１％より多く添加して
も、高分子量化、硬化性の改善の程度は変わらなくなる
。[0008] Tertiary amines used as catalysts include trimethylamine, triethylamine, triethanolamine, and the like. The amount added is suitably 0.3 to 1% based on the total weight of phenols and formaldehyde. If it is too small, the reaction rate for producing phenolic resin will be slow. On the other hand, if the amount is too large, the reaction for producing phenolic resin will become faster and control will become difficult. Further, ammonia is necessary for increasing the molecular weight and improving curability, and the appropriate amount of addition is 0.2 to 1% based on the total weight of both. If the amount is too small, the molecular weight of the produced phenol resin will not be sufficiently high, and the curability will not be improved. Note that even if more than 1% is added, the degree of increase in molecular weight and improvement in curability remains the same.
【０００９】上記レゾール型フェノール樹脂は、直径６
〜１５μｍのガラス繊維のほか、シリカ、ガラスパウダ
、タルク、カオリン、クレー、シリカ、アルミナ等の無
機質充填材、木粉、セルロース粉、硬化したフェノール
樹脂粉等の有機質充填材、添加剤としてカーボンブラッ
ク、スピリットブラック等の着色剤、ステアリン酸亜鉛
、ステアリン酸マグネシウム、ステアリン酸カルシウム
等の離型剤を適宜配合して、ヘンシェルミキサ、ロール
等混練機で混練し、粉砕して成形材料とする。成形材料
とするときには、硬化促進剤として水酸化カルシウムを
添加するが、その量は、材料全体に対して０．５〜１重
量％が好ましい。[0009] The resol type phenolic resin has a diameter of 6
In addition to glass fibers of ~15 μm, inorganic fillers such as silica, glass powder, talc, kaolin, clay, silica, and alumina, organic fillers such as wood flour, cellulose powder, and hardened phenolic resin powder, and carbon black as an additive. , a coloring agent such as spirit black, and a mold release agent such as zinc stearate, magnesium stearate, calcium stearate, etc. are appropriately blended, kneaded with a kneader such as a Henschel mixer or a roll, and pulverized to obtain a molding material. When used as a molding material, calcium hydroxide is added as a hardening accelerator, and the amount thereof is preferably 0.5 to 1% by weight based on the total material.
【００１０】実施例１〜５
表１に示す配合で、フェノールとパラホルムアルデヒド
をトリエチルアミン存在下６０〜８０℃で１〜３時間反
応させ、ついで、アンモニアを添加し、８０〜１００℃
で３〜７時間反応させてレゾール型フェノール樹脂を得
た。上記レゾール型フェノール樹脂に水酸化カルシウム
、ガラス繊維、ガラスパウダ、添加剤を表３に示す配合
で加え、ヘンシェルミキサで混合混練後、乾燥して成形
材料を得た。各成形材料について、３０トン射出成形機
で成形を行ない、硬化性を目視で評価した。結果は、表
４のとおりである。成形には、ＪＩＳ−Ｋ−６９１１に
準じたシャルピー衝撃試験片成形用の金型を用い、金型
温度１８０℃、シリンダ温度（前部：９０℃，後部：５
０℃）とした。Examples 1 to 5 With the formulation shown in Table 1, phenol and paraformaldehyde were reacted in the presence of triethylamine at 60 to 80°C for 1 to 3 hours, then ammonia was added, and the mixture was heated at 80 to 100°C.
The mixture was reacted for 3 to 7 hours to obtain a resol type phenol resin. Calcium hydroxide, glass fiber, glass powder, and additives were added to the above resol type phenolic resin in the formulation shown in Table 3, mixed and kneaded using a Henschel mixer, and then dried to obtain a molding material. Each molding material was molded using a 30-ton injection molding machine, and the curing properties were visually evaluated. The results are shown in Table 4. For molding, a mold for forming Charpy impact test pieces according to JIS-K-6911 was used, with a mold temperature of 180°C and a cylinder temperature (front: 90°C, rear: 5°C).
0°C).
【００１１】比較例１〜６
表２に示す配合で、フェノールとパラホルムアルデヒド
をトリエチルアミン（比較例１〜３）または水酸化カル
シウム（比較例５）またはシュウ酸（比較例６）存在下
６０〜８０℃で１〜３時間反応させ、ついで、アンモニ
ア（比較例１〜２，４〜５）または水酸化カルシウム（
比較例６）を添加し、もしくは添加しない（比較例３）
で８０〜１００℃で３〜７時間反応させてレゾール型フ
ェノール樹脂を得た。以下、実施例と同様にして成形材
料を製造し、特性を評価した。結果を表４に併せて示す
。Comparative Examples 1 to 6 In the formulation shown in Table 2, phenol and paraformaldehyde were mixed in the presence of triethylamine (Comparative Examples 1 to 3), calcium hydroxide (Comparative Example 5), or oxalic acid (Comparative Example 6) at 60 to 80% ℃ for 1 to 3 hours, and then ammonia (Comparative Examples 1 to 2, 4 to 5) or calcium hydroxide (
Comparative Example 6) or not (Comparative Example 3)
The mixture was reacted at 80 to 100°C for 3 to 7 hours to obtain a resol type phenol resin. Hereinafter, molding materials were produced in the same manner as in the examples, and their properties were evaluated. The results are also shown in Table 4.
【００１２】0012
【表１】[Table 1]
【００１３】[0013]
【表２】[Table 2]
【００１４】[0014]
【表３】[Table 3]
【００１５】[0015]
【表４】[Table 4]
【００１６】[0016]
【発明の効果】表４から明らかなように、本発明に係る
方法で製造されたレゾール型フェノール樹脂成形材料は
、未反応フェノールが少なく、シリンダ内の低い温度で
は硬化が進まず安定性を保ち、金型内では速く硬化させ
ることができる。[Effects of the Invention] As is clear from Table 4, the resol type phenolic resin molding material produced by the method according to the present invention has less unreacted phenol and does not harden at low temperatures in the cylinder, maintaining stability. , it can be cured quickly in the mold.
Claims (1)
を１．２〜１．３とし、第３級アミン触媒存在下で第１
段目の反応を行なわせ、その後アンモニア触媒存在下で
第２段目の反応を行なわせてレゾール型フェノール樹脂
を得て、前記レゾール型フェノール樹脂に水酸化カルシ
ウム、充填材を配合して混合混練することを特徴とする
フェノール樹脂成形材料の製造法。Claim 1: The molar ratio of formaldehyde/phenols is 1.2 to 1.3, and the primary
The first step reaction is carried out, and then the second step reaction is carried out in the presence of an ammonia catalyst to obtain a resol type phenol resin, and calcium hydroxide and a filler are blended with the resol type phenol resin and mixed and kneaded. A method for producing a phenolic resin molding material, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8430291A JPH04318053A (en) | 1991-04-17 | 1991-04-17 | Production of phenolic resin molding material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8430291A JPH04318053A (en) | 1991-04-17 | 1991-04-17 | Production of phenolic resin molding material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04318053A true JPH04318053A (en) | 1992-11-09 |
Family
ID=13826690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8430291A Pending JPH04318053A (en) | 1991-04-17 | 1991-04-17 | Production of phenolic resin molding material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04318053A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015169A1 (en) * | 1993-05-12 | 1996-05-23 | Commonwealth Scientific And Industrial Research Organisation | Resins |
| RU2741989C1 (en) * | 2020-04-21 | 2021-02-01 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Вятский государственный университет" | Acid-and-alkali polymer composition for protection of equipment and building structures |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5490293A (en) * | 1977-12-27 | 1979-07-17 | Shin Kobe Electric Machinery | Preparation of phenol resin for laminate |
| JPS62275151A (en) * | 1986-05-23 | 1987-11-30 | Fudo Kagaku Kogyo Kk | Heat-resistant, high-strengh phenolic resin molding material and production thereof |
| JPH02265948A (en) * | 1989-04-07 | 1990-10-30 | Sumitomo Durez Co Ltd | Phenolic resin molding material |
-
1991
- 1991-04-17 JP JP8430291A patent/JPH04318053A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5490293A (en) * | 1977-12-27 | 1979-07-17 | Shin Kobe Electric Machinery | Preparation of phenol resin for laminate |
| JPS62275151A (en) * | 1986-05-23 | 1987-11-30 | Fudo Kagaku Kogyo Kk | Heat-resistant, high-strengh phenolic resin molding material and production thereof |
| JPH02265948A (en) * | 1989-04-07 | 1990-10-30 | Sumitomo Durez Co Ltd | Phenolic resin molding material |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015169A1 (en) * | 1993-05-12 | 1996-05-23 | Commonwealth Scientific And Industrial Research Organisation | Resins |
| RU2741989C1 (en) * | 2020-04-21 | 2021-02-01 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Вятский государственный университет" | Acid-and-alkali polymer composition for protection of equipment and building structures |
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